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From magnificent losers to plucky mavericks and billionaire buccaneers, the America’s Cup has attracted larger-than-life personalities for more than 160 years, explains Keith Dovkants... If we look at the long saga of the America’s Cup we see layer upon layer of colourful history laid down by the remarkable individuals who vied with each other to win it. The Earl of Wilton, commodore of the Royal Yacht Squadron, began it all in 1851 when he invited his opposite number at the New York Yacht Club to visit the famous clubhouse at Cowes. John Cox Stevens accepted with alacrity, suggesting he and his friends bring a yacht, adding that they would “take with good grace the sound thrashing we are likely to get”. The boat was America (pictured above), a schooner that was to lend its name to the oldest international trophy in sport. Stevens was a larger-than-life, high-rolling gambler (his family owned Hoboken, New Jersey) and he planned to wager a huge sum on America beating the British opposition, but there was no enthusiasm for big stakes and he returned home with modest winnings and the RYS’s “Cup of One Hundred Sovereigns”, often (and mistakenly) known as the 100 Guinea Cup. It was enough. America hailed Stevens and his syndicate heroes and moves were made to make the Cup a permanent challenge trophy.

From magnificent losers to plucky mavericks and billionaire buccaneers, the America’s Cup has attracted larger-than-life personalities for more than 160 years, explains Keith Dovkants...

If we look at the long saga of the America’s Cup we see layer upon layer of colourful history laid down by the remarkable individuals who vied with each other to win it. The Earl of Wilton, commodore of the Royal Yacht Squadron, began it all in 1851 when he invited his opposite number at the New York Yacht Club to visit the famous clubhouse at Cowes. John Cox Stevens accepted with alacrity, suggesting he and his friends bring a yacht, adding that they would “take with good grace the sound thrashing we are likely to get”.

The boat was America (pictured above), a schooner that was to lend its name to the oldest international trophy in sport. Stevens was a larger-than-life, high-rolling gambler (his family owned Hoboken, New Jersey) and he planned to wager a huge sum on America beating the British opposition, but there was no enthusiasm for big stakes and he returned home with modest winnings and the RYS’s “Cup of One Hundred Sovereigns”, often (and mistakenly) known as the 100 Guinea Cup.

It was enough. America hailed Stevens and his syndicate heroes and moves were made to make the Cup a permanent challenge trophy.

2 - William Henn and Peggy the monkey William Henn and Peggy the monkey

The American Civil War intervened, but soon after it ended in 1865 challengers appeared. Several yachts from Britain and Canada tried and failed to beat the American defenders, the most notable of which was Galatea. There was great affection for her owner William Henn, a wealthy former naval officer from Scotland who crossed the Atlantic in his gaff-rigged cutter accompanied Mrs Henn, their five dogs and a pet monkey, Peggy, who was adept at sail handling. Galatea’s fabulous interior, with mahogany panelling, fireplaces, potted plants and leopard skin rug, was left virtually intact for racing. She was thrashed in the 1886 America's Cup, but Henn was a great sport and took it so well he made many friends. When Peggy died, four American yacht skippers carried her coffin.

The American Civil War intervened, but soon after it ended in 1865 challengers appeared. Several yachts from Britain and Canada tried and failed to beat the American defenders, the most notable of which was Galatea.

There was great affection for her owner William Henn, a wealthy former naval officer from Scotland who crossed the Atlantic in his gaff-rigged cutter accompanied Mrs Henn, their five dogs and a pet monkey, Peggy, who was adept at sail handling. Galatea’s fabulous interior, with mahogany panelling, fireplaces, potted plants and leopard skin rug, was left virtually intact for racing. She was thrashed in the 1886 America's Cup, but Henn was a great sport and took it so well he made many friends. When Peggy died, four American yacht skippers carried her coffin.

In 1893 Lord Dunraven launched his first bid for the America's Cup. A vastly rich landowner and passionately keen yachtsman, Dunraven's entry Valkyrie III was reckoned to be a match for anything the Americans had. A two-time loser, Dunraven caused great uproar in 1895 when he suggested he was being cheated. He accused the defender of “irregular behaviour”, suspecting she was shipping extra ballast after measurement, and demanded an investigation. The verdict went against him and he returned home in a huff, never to compete in international racing again. The affair added another element to the Cup’s charisma that prevails to this day — controversy.

In 1893 Lord Dunraven launched his first bid for the America's Cup. A vastly rich landowner and passionately keen yachtsman, Dunraven's entry Valkyrie III was reckoned to be a match for anything the Americans had.

A two-time loser, Dunraven caused great uproar in 1895 when he suggested he was being cheated. He accused the defender of “irregular behaviour”, suspecting she was shipping extra ballast after measurement, and demanded an investigation.

The verdict went against him and he returned home in a huff, never to compete in international racing again. The affair added another element to the Cup’s charisma that prevails to this day — controversy.

In the words of Sir Thomas Lipton, the America’s Cup was “the most elusive piece of metal in all the world”. He should know. The grocery tycoon launched no fewer than five attempts to capture it, all in vain. Sir Thomas, a canny Scot, spent vast resources of money, energy and time in pursuit of what he called “the Auld Mug”, causing many to question why a man of his acknowledged acuity would chase an apparently impossible dream. Lipton turned his parents’ corner shop in Glasgow into a corporate colossus that straddled the empire. He was a close friend of the Prince of Wales, later Edward VII, and although all five of his yachts, all called Shamrock (he was of Ulster-Irish descent), were soundly beaten by the New York Yacht Club defenders between 1899 and 1930, the Americans took him to their hearts. The genial Sir Thomas was presented with a special cup for being “the best of all losers”.

In the words of Sir Thomas Lipton, the America’s Cup was “the most elusive piece of metal in all the world”. He should know. The grocery tycoon launched no fewer than five attempts to capture it, all in vain.

Sir Thomas, a canny Scot, spent vast resources of money, energy and time in pursuit of what he called “the Auld Mug”, causing many to question why a man of his acknowledged acuity would chase an apparently impossible dream.

Lipton turned his parents’ corner shop in Glasgow into a corporate colossus that straddled the empire. He was a close friend of the Prince of Wales, later Edward VII, and although all five of his yachts, all called Shamrock (he was of Ulster-Irish descent), were soundly beaten by the New York Yacht Club defenders between 1899 and 1930, the Americans took him to their hearts. The genial Sir Thomas was presented with a special cup for being “the best of all losers”.

“Bondy”, as he was known, was born in London and emigrated to Australia with his parents in 1950, aged 12. He was a signwriter by trade but speculated in property and by the 1970s had a business empire based in Fremantle. Australian media magnate Sir Frank Packer had had a stab at the Cup by then, without success, and Bond resolved to launch a challenge of his own. Bondy was no great sailor but his drive and personality were unstoppable. In New York’s Studio 54 one night he got up to ask a leggy model to dance. “I thought you were taller,” she sniffed. “You should see me when I stand on my wallet,” Bondy returned. He was certainly rich. He piled money into three doomed challenges, losing in 1977 to Ted Turner.

“Bondy”, as he was known, was born in London and emigrated to Australia with his parents in 1950, aged 12. He was a signwriter by trade but speculated in property and by the 1970s had a business empire based in Fremantle.

Australian media magnate Sir Frank Packer had had a stab at the Cup by then, without success, and Bond resolved to launch a challenge of his own. Bondy was no great sailor but his drive and personality were unstoppable.

In New York’s Studio 54 one night he got up to ask a leggy model to dance. “I thought you were taller,” she sniffed. “You should see me when I stand on my wallet,” Bondy returned. He was certainly rich. He piled money into three doomed challenges, losing in 1977 to Ted Turner.

Winner of the 1980 America’s Cup, Dennis Conner was probably the most gifted sailor of the age and is still known as “Mr America’s Cup”. He elicited gasps from the crowd one Cowes Week when, as guest helmsman, Conner steered a maxi on a beam reach under full plain sail up the Medina River, doing better than 10 knots, then spun the 25 metre boat through 180 degrees and sailed back into the Solent on the opposite tack. With Conner skippering the defender, the New York Yacht Club thought, quite reasonably, that the America’s Cup was perfectly safe bolted down on the plinth it had occupied for more than 130 years. The New York Yacht Club grandees reckoned without Bond’s designer, Ben Lexcen. When Bond returned to challenge in 1983 with Australia II, the yacht had an innovative feature — a winged keel. Lexcen had developed the design in secret and Australia went on to win the Cup. Conner, distraught, said later: “It was like losing the Panama Canal.”

Winner of the 1980 America’s Cup, Dennis Conner was probably the most gifted sailor of the age and is still known as “Mr America’s Cup”. He elicited gasps from the crowd one Cowes Week when, as guest helmsman, Conner steered a maxi on a beam reach under full plain sail up the Medina River, doing better than 10 knots, then spun the 25 metre boat through 180 degrees and sailed back into the Solent on the opposite tack.

With Conner skippering the defender, the New York Yacht Club thought, quite reasonably, that the America’s Cup was perfectly safe bolted down on the plinth it had occupied for more than 130 years. The New York Yacht Club grandees reckoned without Bond’s designer, Ben Lexcen.

When Bond returned to challenge in 1983 with Australia II, the yacht had an innovative feature — a winged keel. Lexcen had developed the design in secret and Australia went on to win the Cup. Conner, distraught, said later: “It was like losing the Panama Canal.”

A challenger in 1983, Peter de Savary is a British entrepreneur who put together a campaign with the help of friends and sponsors. Their boat, Victory 83, was reckoned to be the best British effort anyone could remember, but she was ultimately beaten by Australia II, the winning boat. “We put up a credible show,” De Savary recently told Boat International. “It took a lot of effort and cost a lot of money, but looking back I have nothing but fond memories.” De Savary, whose business interests include luxury hotels and resorts, thinks the America’s Cup entices a certain kind of person. “It’s like Everest,” he says. “It’s the biggest and greatest challenge if you are a sailor. There is no buzz like it and if you have something of the buccaneer about you, which I do, then it’s irresistible. And people remember. I was in a London cab the other day and the cabbie said: ‘Aren’t you that bloke who did the America’s Cup?’” The America’s Cup may be no more than an Auld Mug, but the memory of those exceptional individuals is forever alloyed into the silver.

A challenger in 1983, Peter de Savary is a British entrepreneur who put together a campaign with the help of friends and sponsors. Their boat, Victory 83, was reckoned to be the best British effort anyone could remember, but she was ultimately beaten by Australia II, the winning boat.

“We put up a credible show,” De Savary recently told Boat International. “It took a lot of effort and cost a lot of money, but looking back I have nothing but fond memories.”

De Savary, whose business interests include luxury hotels and resorts, thinks the America’s Cup entices a certain kind of person. “It’s like Everest,” he says. “It’s the biggest and greatest challenge if you are a sailor. There is no buzz like it and if you have something of the buccaneer about you, which I do, then it’s irresistible. And people remember. I was in a London cab the other day and the cabbie said: ‘Aren’t you that bloke who did the America’s Cup?’”

The America’s Cup may be no more than an Auld Mug, but the memory of those exceptional individuals is forever alloyed into the silver.

The colourful characters who built the legend of the America’s Cup

John Cox Stevens

From magnificent losers to plucky mavericks and billionaire buccaneers, the America’s Cup has attracted larger-than-life personalities for more than 160 years, explains Keith Dovkants...

If we look at the long saga of the America’s Cup we see layer upon layer of colourful history laid down by the remarkable individuals who vied with each other to win it. The Earl of Wilton, commodore of the Royal Yacht Squadron, began it all in 1851 when he invited his opposite number at the New York Yacht Club to visit the famous clubhouse at Cowes. John Cox Stevens accepted with alacrity, suggesting he and his friends bring a yacht, adding that they would “take with good grace the sound thrashing we are likely to get”.

The boat was America (pictured above), a schooner that was to lend its name to the oldest international trophy in sport. Stevens was a larger-than-life, high-rolling gambler (his family owned Hoboken, New Jersey) and he planned to wager a huge sum on America beating the British opposition, but there was no enthusiasm for big stakes and he returned home with modest winnings and the RYS’s “Cup of One Hundred Sovereigns”, often (and mistakenly) known as the 100 Guinea Cup.

It was enough. America hailed Stevens and his syndicate heroes and moves were made to make the Cup a permanent challenge trophy.

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